City Guide
Portland, Oregon
Four places in Portland that prove the city's reputation for the strange is well earned. Start with the Shanghai Tunnels to see the dark history buried under the streets. We've also included one hotel that actually captures the local design scene.
At a glance: 4 place guides, 1 hand-picked hotel, vibes that skew historic and hidden gem.
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Our picks in Portland
Ranked. Start at the top and work down as far as your weekend allows.
- 1
Portland's Shanghai Tunnels: The City's Buried Underworld
Trapdoors and smuggling routes cut through the dirt beneath Old Town. You get the story of the city at its roughest, where men were allegedly forced into service at sea.
- 2
Witch’s Castle: Portland’s Moss-Covered Ruins and Dark History
Moss covers the stone remains of a 1930s park station in the middle of the woods. It sits on the site of a 19th-century murder, making it the city's most haunted hike.
- 3
The Grotto: A Cliffside Sanctuary and Botanical Escape
A sanctuary carved into a basalt cliff that rises sixty-two acres above the street. The gardens blend spiritual architecture with the local greenery.
- 4
Freakybuttrue Peculiarium: Portland's Cabinet of Gross Curiosities
Gross artifacts and creepy exhibits fill this dense collection of the unsettling. It is the best place to find the rare things most museums would throw away.
Where we'd actually stay
Know before you go
Tri-met bus 12 stops at NE Sandy and 84th for the cliffside shrine. If you head to the forest ruins, the walk from Upper Macleay is half a mile. Underground tours require booking in advance because group sizes are kept small. Wear shoes that can handle uneven ground and low ceilings in the tunnels.
Common questions about Portland
Which spot should we visit first?
The Shanghai Tunnels set the tone for the rest of the city. It is the best way to understand the grit that existed before the modern boutiques arrived.
Are the forest ruins hard to find?
Not if you use the Aspen trail or enter from Thurman Street. You can choose between a short walk from the upper lot or a longer stroll from NW 30th and Upshur.
Can we see the whole cliffside sanctuary for free?
You can enter the grounds, but the upper garden requires a ticket. Buy yours at the gift shop building near the entrance.
Is the oddities museum family-friendly?
It depends on your family. The exhibits are intentionally stomach-turning and some people find the collection genuinely creepy.